Total Synthesis of Brevetoxin-B
Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique...
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| Veröffentlicht in: | Journal of the American Chemical Society 2004-11, Vol.126 (44), p.14374-14376 |
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| container_end_page | 14376 |
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| container_issue | 44 |
| container_start_page | 14374 |
| container_title | Journal of the American Chemical Society |
| container_volume | 126 |
| creator | Matsuo, Goh Kawamura, Koji Hori, Nobuyuki Matsukura, Hiroko Nakata, Tadashi |
| description | Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique, complex structure and potent biological activity have attracted the attention of synthetic organic chemists. Total synthesis of BTX-B has been accomplished via the coupling of the ABCDEFG and IJK-ring segments, each ether ring of which was stereoselectively and efficiently constructed on the basis of SmI2-induced intramolecular cyclization, 6-endo-cyclization of hydroxy epoxide, ring-closing olefin metathesis, and SmI2-induced intramolecular Reformatsky-type reaction. Several kinds of double reactions at the left and right sides were efficiently used through the synthesis. |
| doi_str_mv | 10.1021/ja0449269 |
| format | Article |
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The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique, complex structure and potent biological activity have attracted the attention of synthetic organic chemists. Total synthesis of BTX-B has been accomplished via the coupling of the ABCDEFG and IJK-ring segments, each ether ring of which was stereoselectively and efficiently constructed on the basis of SmI2-induced intramolecular cyclization, 6-endo-cyclization of hydroxy epoxide, ring-closing olefin metathesis, and SmI2-induced intramolecular Reformatsky-type reaction. 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Am. Chem. Soc</addtitle><description>Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique, complex structure and potent biological activity have attracted the attention of synthetic organic chemists. Total synthesis of BTX-B has been accomplished via the coupling of the ABCDEFG and IJK-ring segments, each ether ring of which was stereoselectively and efficiently constructed on the basis of SmI2-induced intramolecular cyclization, 6-endo-cyclization of hydroxy epoxide, ring-closing olefin metathesis, and SmI2-induced intramolecular Reformatsky-type reaction. Several kinds of double reactions at the left and right sides were efficiently used through the synthesis.</description><subject>Animals</subject><subject>Chemistry</subject><subject>Dinoflagellida - chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Marine Toxins - chemical synthesis</subject><subject>Organic chemistry</subject><subject>Oxocins - chemical synthesis</subject><subject>Preparations and properties</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1PwkAQBuCN0QiiB_-AcvHgoTqzX-0epX5GVBLwvNlut7EILdktBv69NRC4eNpM9smbeYeQc4QbBIq3UwOcKyrVAemioBAJpPKQdAGARnEiWYechDBtR04TPCYdFIJiLESXXE7qxsz643XVfLlQhn5d9Afe_bimXpVVNDglR4WZBXe2fXvk8_Fhkj5Hw4-nl_RuGBkWqyZCsBytzF3BnEqUUFY64AyT2HKeZ8hiBpJluRSGF0KZTGYODVfGAiongfXI9SbX-joE7wq98OXc-LVG0H8l9a5kay82drHM5i7fy22rFlxtgQnWzApvKluGvZO0DeK8ddHGlaFxq92_8d9axiwWejIa63cY3b-9gtDpPtfYoKf10lftSf5Z8BcxjXFt</recordid><startdate>20041110</startdate><enddate>20041110</enddate><creator>Matsuo, Goh</creator><creator>Kawamura, Koji</creator><creator>Hori, Nobuyuki</creator><creator>Matsukura, Hiroko</creator><creator>Nakata, Tadashi</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20041110</creationdate><title>Total Synthesis of Brevetoxin-B</title><author>Matsuo, Goh ; Kawamura, Koji ; Hori, Nobuyuki ; Matsukura, Hiroko ; Nakata, Tadashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-10c41c6def3e98959c6e043187c44db1373063bd65a4f59ab6be1a49ac019e603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Animals</topic><topic>Chemistry</topic><topic>Dinoflagellida - chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Marine Toxins - chemical synthesis</topic><topic>Organic chemistry</topic><topic>Oxocins - chemical synthesis</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsuo, Goh</creatorcontrib><creatorcontrib>Kawamura, Koji</creatorcontrib><creatorcontrib>Hori, Nobuyuki</creatorcontrib><creatorcontrib>Matsukura, Hiroko</creatorcontrib><creatorcontrib>Nakata, Tadashi</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsuo, Goh</au><au>Kawamura, Koji</au><au>Hori, Nobuyuki</au><au>Matsukura, Hiroko</au><au>Nakata, Tadashi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Brevetoxin-B</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2004-11-10</date><risdate>2004</risdate><volume>126</volume><issue>44</issue><spage>14374</spage><epage>14376</epage><pages>14374-14376</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether ring system with 23 stereocenters. Its unique, complex structure and potent biological activity have attracted the attention of synthetic organic chemists. Total synthesis of BTX-B has been accomplished via the coupling of the ABCDEFG and IJK-ring segments, each ether ring of which was stereoselectively and efficiently constructed on the basis of SmI2-induced intramolecular cyclization, 6-endo-cyclization of hydroxy epoxide, ring-closing olefin metathesis, and SmI2-induced intramolecular Reformatsky-type reaction. Several kinds of double reactions at the left and right sides were efficiently used through the synthesis.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15521755</pmid><doi>10.1021/ja0449269</doi><tpages>3</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Chemistry Dinoflagellida - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Marine Toxins - chemical synthesis Organic chemistry Oxocins - chemical synthesis Preparations and properties |
| title | Total Synthesis of Brevetoxin-B |
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